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Girón RM, Ouyang J, Favereau L, et al. Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy. Org Lett. 2018;20(7):1764-1767doi: 10.1021/acs.orglett.8b00256.
Girón, R. M., Ouyang, J., Favereau, L., Vanthuyne, N., Crassous, J., Filippone, S., & Martín, N. (2018). Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy. Organic letters, 20(7), 1764-1767. https://doi.org/10.1021/acs.orglett.8b00256
Girón, Rosa M, et al. "Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy." Organic letters vol. 20,7 (2018): 1764-1767. doi: https://doi.org/10.1021/acs.orglett.8b00256
Girón RM, Ouyang J, Favereau L, Vanthuyne N, Crassous J, Filippone S, Martín N. Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy. Org Lett. 2018 Apr 06;20(7):1764-1767. doi: 10.1021/acs.orglett.8b00256. Epub 2018 Mar 09. PMID: 29522351.
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Org Lett. 2018 Apr 06;20(7):1764-1767. doi: 10.1021/acs.orglett.8b00256. Epub 2018 Mar 09.

Reversible Stereodivergent Cycloaddition of Racemic Helicenes to [60]Fullerene: A Chiral Resolution Strategy.

Organic letters

Rosa M Girón, Jiangkun Ouyang, Ludovic Favereau, Nicolas Vanthuyne, Jeanne Crassous, Salvatore Filippone, Nazario Martín

Affiliations

  1. Departamento de Química Orgánica , Universidad Complutense de Madrid , Avda. Complutense s/n , E-28040 Madrid , Spain.
  2. Institut des Sciences Chimiques de Rennes UMR 6226 CNRS - Univ. Rennes , Campus Beaulieu , Rennes 35042 Cedex , France.
  3. Aix Marseille University , CNRS, Centrale Marseille, iSm2, UMR 7313 , Marseille , France.
  4. IMDEA-Nanociencia, C/Faraday, 9, Campus de Cantoblanco , E-28049 Madrid , Spain.

PMID: 29522351 DOI: 10.1021/acs.orglett.8b00256

Abstract

[60]Fullerene and its rarely explored reversible covalent chemistry have been harnessed as an efficient alternative for the chiral resolution of racemates. By using only catalytic amounts of chiral agents, stereodivergent 1,3-dipolar cycloadditions of racemic helicenes onto [60]fullerene were carried out. The formed helicene/fullerene diastereomers were easily separated by conventional chromatography, and afterward, a simple catalyzed 1,3-dipolar retro-cycloaddition afforded helicene starting materials in high optical purity.

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